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Verification of Biaryl-Structure Axial Chirality Produced in Ellagitannins by Chemical Oxidation
Shinnosuke Wakamori1, Rumi Osada1, Shintaro Matsumoto1
1School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo 669-1337, Japan.
Abstract:
The axial chirality of hexahydroxydiphenoyl (HHDP) groups contained in ellagitannins depends on the bridging position of d-glucose. The 4,6-O-HHDP group predominantly exhibits S-type chirality. This study elucidated the formation of the 4,6-O-(R)-HHDP group and subsequent axial isomerization by means of oxidative coupling of galloyl groups, which resulted in S chirality.
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